Methyl iodide → methyl 3-cyclohex-1-en-1-yl-1H-indole-6-carboxylate

HRID 498997Notes

Reaction equation

[C:1]1([C:7]2[C:15]3[C:10](=[CH:11][C:12]([C:16]([OH:18])=[O:17])=[CH:13][CH:14]=3)[NH:9][CH:8]=2)[CH2:6][CH2:5][CH2:4][CH2:3][CH:2]=1.[C:19]([O-])([O-])=O.[K+].[K+].CI>CN(C=O)C>[C:1]1([C:7]2[C:15]3[C:10](=[CH:11][C:12]([C:16]([O:18][CH3:19])=[O:17])=[CH:13][CH:14]=3)[NH:9][CH:8]=2)[CH2:6][CH2:5][CH2:4][CH2:3][CH:2]=1

Participants

Conditions

Temperature: 20 °C

Procedure

A solution (0.1 M) of 3-cyclohex-1-en-1-yl-1H-indole-6-carboxylic acid (prepared as described in published International patent application WO 2004/087714) in dry DMF was cooled to 0° C. and treated with K2CO3 (1.05 eq). A solution (3 M) of MeI (1.05 eq) in DMF was then added over 0.5 h and the temperature was raised to 20° C. After 18 h the reaction was quenched with aqueous HCl (1 N) and diluted with EtOAc. The organic phase was separated and washed several times with aqueous HCl (1 N), then with brine. The dried organics were concentrated to give the title compound (99%) as a solid; (ES+) m/z 256 (M+H)+.

Workup

customAfter 18 h the reaction was quenched with aqueous HCl (1 N)
additiondiluted with EtOAc
customThe organic phase was separated
washwashed several times with aqueous HCl (1 N)
concentrationThe dried organics were concentrated

Sources & evidence

ORD record: ord-d1a3874628da4a0d885e2c42b824ad6a
Source dataset: uspto-grants-2010_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07767660B2

Reaction notes

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